title: Iodocyclization and Prins-type macrocyclization: an efficient formal synthesis of leucascandrolide A.
abstract: The formal total synthesis of leucascandrolide A has been achieved in 20 steps from a known epoxide with an overall yield of 11.5% following a recently developed strategy for the construction of trans-2,6-disubstituted-3,4-dihydropyrans and a Lewis acid catalyzed intramolecular Prins-cyclization of an aldehydic homoallylic alcohol to generate the tetrahydropyran ring with three stereogenic centers and macrocycle concomitantly.
authors.affiliation: Organic Chemistry Division I, Indian Institute of Chemical Technology, CSIR, Hyderabad 500 607, India.
authors.forename: J S
authors.initials: JS
authors.lastname: Yadav
authors.forename: Manas R
authors.initials: MR
authors.lastname: Pattanayak
authors.forename: Pragna P
authors.initials: PP
authors.lastname: Das
authors.forename: Debendra K
authors.initials: DK
authors.lastname: Mohapatra
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis*
chemical_list: D007211:Indoles; D058116:Lewis Acids; D047028:Macrocyclic Compounds; D012717:Sesquiterpenes; C408748:leucascandrolide A; C030374:indole